Blah blah blah! You're silly if you think your going time it just right and pick the perfect regional to go to. Every single new hire who is hired before you, beat you. Yes you need letters of rec, there's some who just will not upgrade.
Don't stand on the sidelines too long and think, it's called paralysis from over analysis. Throw your hat into the ring and get on with the show if your serious. There's plenty of others who are saying yes and getting in ahead of you.
I wouldn't worry about street captains, perhaps some Skywest or Envoy people who are sick of being on the 8 to 10 year upgrade path will jump ship to get a 1000 tpic and bail out as quickly as they can.
We will get more flying, key is, you want to be at the airline before they announce it.
I'll say it again, everything is **** luck.